Hydrochloric Acid → (S)-2-amino-4-cyclohexylbutanoic acid

HRID 478044Notes

Reaction equation

HRID 478044 reaction equation
[NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl>O>[NH2:1][C@@H:2]([CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 2724505(S)-2-amino-4-phenylbutanoic acid

Product 1

HCID 22839041(S)-2-amino-4-cyclohexylbutanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

896 mg of L-homophenylalanine (2(S)-amino-4-phenylbutyric acid) are hydrogenated in 25 ml of water and 5.5 ml of 1N HCl in the presence of 18 mg of Nishimura catalyst (rhodium oxide/platinum oxide). The reaction mixture is filtered while warm. The title compound crystallises out of the filtrate in the form of white crystals after the addition of 5.5 ml of 1N NaOH. M.p. 265°-266°; Rf (R)=0.09.

Workup

  1. filtrationThe reaction mixture is filtered
  2. temperaturewhile warm
  3. customThe title compound crystallises out of the filtrate in the form of white crystals
  4. additionafter the addition of 5.5 ml of 1N NaOH

Sources & evidence

ORD record
ord-d5ed0b0ee166421786fc06ce4f30a4a7
Source dataset
uspto-grants-1989_12
Patent number
US04889869

Reaction notes

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